


It's Educational

by JackTrades



Series: Married Destiel verse [2]
Category: Supernatural
Genre: AU, AU human, Anal Sex, Destiel - Freeform, Established Relationship, M/M, Married Couple, New Year's Resolutions, Threesome, probably traumatizing the neighbors
Language: English
Status: Completed
Published: 2016-01-09
Updated: 2016-01-09
Packaged: 2018-05-12 16:34:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 7,929
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5672785
Author URL: https://archiveofourown.org/users/JackTrades/pseuds/JackTrades
Summary: <blockquote class="userstuff">
              <p>Dean and Castiel offer to educate Benny on the ins and outs of gay sex</p>
            </blockquote>





	1. The Proposal

**Author's Note:**

> Written for Naughty New Years! Destiel Fic Competition!

Dean walks in the front door of the condo with much more zeal than usual. Castiel couldn't see him but he hears it in the way Dean is walking. Castiel is in the kitchen on the second floor looking over a cookbook trying to decide what to make for dinner. He knows Dean had plans to grab a few beers with Benny when Dean got out of work at the auto body shop today. Frankly, he is surprised that Dean was home this early. Those two usually plan this around Benny’s day off and Dean's earlier days. Usually it is poker or strip clubs or some other unsavory thing Castiel wants nothing to do with. He trusts his husband. He has to smile to himself when he thinks that.

 

Dean comes up behind him and wraps his hands around Castiel’s waist. He hooks his chin on Castiel’s shoulder. “Hey sexy, is that my dinner?”

 

Castiel smiles but doesn't turn to him yet, “Maybe. You're home early. I thought you would be at it for hours and taking an Uber home.”

 

Dean chuckles. It reverberates through Castiel and makes him shiver. “He got called into work. One of the other bouncers called out and they're understaffed.”

 

“So you didn't get your fill of shenanigans then?”

 

Dean gives Castiel a quick peck on the cheek and pulls away. He leans against the counter with a serious look on his face. “Nah. He actually wanted to talk to me about something personal. Something that couldn't wait until poker night next week.”

 

Castiel feels his stomach drop. He is bracing himself, “Oh God, is he alright?”

 

Dean is confused. “What? Yeah, he's fine it's just that he wanted some advice. Turns out that he's sorta into men too.”

 

“I knew it!” Castiel slaps him on the arm. “Jesus, Dean, you had me thinking that he had cancer or something!”

 

“Why do you always go to the worst case scenario?! Don't answer that. Anyway,” Dean stands up straighter, “I guess he got hit on by some twink at the club and decided to give it a shot. Now he's having a personal crisis because he only ever had sex with women and this whole men thing is throwing him for a loop.”

 

Castiel rolls his eyes, "First of all, he had sex with a _boy_. You and I both know some twink is nothing compared to a full grown man! Second, did he enjoy it? What did you tell him?”

 

Dean laughs, “I told him, first off, that if he feels like he might be attracted to men that he should have sex with a _man,_ not some teenager.” Now Castiel is laughing too. This is why they worked as a couple: mutual love of ball busting. Dean sidles closer to Castiel and drops his voice lower, "I told him that he needed to find a hot, sexy, full grown man. One with a good body that could fuck like there's no tomorrow.”

 

Castiel pulls him by his belt into his own body. He slots a leg between Dean's and gives a teasing rub as he runs his hands up and down on Dean's flanks, “Yeah? What else did tell Benny?”

 

Dean moans and grabs Castiel’s ass. He pulls the other man harder into himself. Dean smirks when he gets a gasp for his efforts, “Told him that he has to do it right. Told him to use lots of lube and condoms. And I told him there's nothing better than opening up a guy nice and slow, making him beg for it, then pumping your dick into him while you use his hip bones like they're handlebars…”

 

The rest of that conversation is cut off. Castiel pulls Dean in for a heated kiss. Dean responds by lifting Castiel by his ass to sit him on the counter. Dean leaves his mouth to trail sloppy kisses down Castiel’s neck as he works off his blue tie and starts unbuttoning his shirt. Dean always loves to lick across newly revealed flesh when he is with Castiel. Castiel groans, "We should move this to the bedroom. The neighbors are going to complain again if we have sex in front of the window.”

 

Dean pauses his progress just long enough to say, “Fuck the neighbors.”

 

Castiel hopes for that response. He reaches down and yanks Dean's ratty tee shirt off. He can't access any other clothing to remove it from this position. He loves being at Dean's mercy like this. He can check his brain out and he knows Dean will take care of him. It is a break from his professional role as the Division Branch Head for the Logistics Analysis Department. No barking orders or making decisions or interns that seem to multiply by the hour. Although sex interns could be fun. Heh, sex interns. He hadn't meant to laugh out loud from his thought. Dean pulls back grinning, “Something funny?”

 

Castiel blushes, "I was just thinking about how you take such good care of me. And that it's nice to not have to make the decisions…”

 

Dean's grin widens, "And?”

 

Castiel huffs. He knows he will get ribbed for this one, “And that it's nice to get a break from being in charge and having interns. Then I thought sex interns could be fun to have.”

 

Dean barks out a laugh. Thankfully he leans into Castiel’s shoulder to muffle some of it. “Seriously? You think about the weirdest shit at inappropriate times.”

 

Castiel leans back annoyed, "I have killed the mood, haven't I?”

 

Dean tries to stop laughing but fails, “I'm still in the mood, baby.”

 

Castiel crosses his arms, “Yeah but before it was all sexy talk and now you're laughing at me.”

 

Dean cups his face and mocks, “Awwww, don't pout.” He fully expects that icy glare he gets in response. He lets go of Castiel’s face and goes for Castiel’s belt, “I think you're still in the mood too.” Dean unbuckles the belt and slowly pulls it out of the belt loops. “You're just mad. That's okay. I can have mad sex with you.” Castiel’s glare softens just enough to convince Dean to continue. He pops the clasp of his dress pants and moves over to the button, purposely dragging his knuckles across Castiel’s stomach in that way that makes him squirm. He drags the zipper down painstakingly slow. Once it is all the way down, he slips his hand into Castiel’s pants to knead his erection through his thin briefs. Dean bites his lip and put on his best smolder, not breaking eye contact with Castiel. Castiel moans, uncrosses his arms and puts them on Dean's shoulders. He grips hard and Dean palms just a bit harder. “There ya go,” Dean sounds wrecked already. He keeps his hand going while the other wanders over Castiel’s body to the dress shirt. He gently pushes it out of the way and kisses along his skin as it is revealed. Dean ghosts over to Castiel’s ear, “Do we still have lube in one of the drawers down here?”

 

Castiel pants, "In the glass cabinet next to the emergency cash.” Dean raises an eyebrow. Castiel pulls a face, "What? It doesn't belong in the junk drawer!”

 

Dean stifles his laugh and walks to the cabinet. The half used tube of lubricant is right in front like Castiel said it would be. Dean unbuckles his own belt and drops his jeans. His erection tents his boxer briefs as he walks back over to Castiel. It is times like this that Dean is grateful for the ‘no shoes in the house’ rule. And grateful for heated kitchen floors. He pulls Castiel into a soft kiss before stepping back. “Okay baby, assume the position.” He gestures his arms wide open.

 

Castiel rolls his eyes and hops off the counter. He turns his back to Dean and braces his hands on the cool countertop. Dean places the lube on the counter and runs his hands down Castiel’s arms while he kisses over his shoulder blades. Castiel moans, “Dean, I'm not in the mood for teasing tonight.”

 

Dean plasters his body to Castiel’s back and leans against his neck. “Why? Because it's a school night?”

 

Castiel lets out a huff, “Yes. I have a meeting at eight tomorrow with that asshole from Headquarters.”

 

Dean lets his hands roam over the front of Castiel while he grinds small circles against his ass. “Tell one of your sex interns to cover it.” That earns him an elbow to the side. “Ow! Fine. This will be a quickie, boss man.” Dean promptly drops to his knees and drags down Castiel’s underwear with him. He taps the back of Castiel’s knee to signal him to lift his foot. Once one side was free, Castiel kicks them off the other foot. Dean leans back on his haunches, “Look at that ass…” He punctuates it with a firm slap on the side of his ass. He grabs both cheeks and moans to himself as he pulls them apart. “I know you have a meeting tomorrow, but do you have any objection to me eating you out?”

 

Castiel pushes the lube onto the floor and watches it land in Dean's general vicinity. He throws a playful look over his shoulder. “Before dinner?”

 

Dean moans, “I could eat you for breakfast, lunch, and dinner…”

 

“As much as we would both enjoy it, not tonight.” Castiel ignores Dean's pout.

 

“Fine. You're making it up to me on Friday though!” Dean picks up the lube and stands up. He squirts a generous amount on his fingers and swipes it over Castiel’s hole. Castiel yelps from the sudden coldness of it. Dean slaps his ass again. “What? Need me to slow down?”

 

So that's how it is going to be? Castiel knows how to handle that. “Nothing I can't handle.” He looks at Dean with challenge in his eyes.

 

Dean hates that look. He always wants to fuck that look right off his face. He taps his fingers over Castiel’s perineum quickly under Castiel squirms but eventually lets out the noises he desperately tries to keep in. “Yeah? Doesn't look like you're handling much right now.” Dean jams a finger into Castiel up to the first knuckle to cut off any mouthy response he may formulate. He pumps it in and out a few times before he adds a second to the mix. He knows Castiel’s body almost as well as his own at this point. He knows Castiel can handle it. He scissors his fingers and purposely brushes over Castiel’s prostate. Castiel is stubbornly holding back his noises again in protest. Dean brings his free hand to Castiel’s perineum and starts swatting it lightly as he rubs inside.

 

The noise he gets in reward is barely human. Castiel’s head falls forward and his arms tremble. “Fuck! Dean, I'm going to come if you keep that up!” Dean grins wide and gives a couple more taps. Just enough to rip a high-pitched keening noise from Castiel.

 

Dean pulls out of him and yanks his own boxers down. He lets Castiel recover while Dean slicks his own dick. "That enough prep or do you need three tonight?” Dean is genuine with his concern. He always asks. It didn't matter how many times they had sex, he always asks.

 

Castiel pants a few times trying to compose himself. “I'm good. I'm not going to last long though.”

 

Dean chuckles, "Good. Come here.” He holds an arm out. Castiel immediately pulls himself up and stands in front of Dean with their chests almost touching. Dean runs a hand through Castiel’s hair to get it out of his face. "You're gorgeous. You know that, right?” Castiel blushes and looks away. “Hey, do you think Benny could be our sex intern?”

 

“Dean!”

 

“Come on, hear me out.” Dean hugs Castiel as he guides Castiel back to the counter. If the nosey neighbors are going to look in the windows, he's going to give them a hell of an eyeful. “I was just thinking that the guy has a lot to learn.” Dean lifts Castiel so he is halfway sitting on the counter and needs to hold onto Dean for balance. He grips himself and guides towards Castiel’s hole. “I was just thinking about how hot his fingers would look spreading you open…” Dean thrusts into Castiel and doesn't stop until he bottoms out. It punches a long groan out of both men. "He's got those huge hands. Bet you two of his fingers would feel like three or four of mine.”

 

Castiel digs his heels into Dean's lower back. “Fuck, Dean, your dirty mind…” Castiel is a sucker for dirty talk during sex.

 

Dean starts a slow pace to let Castiel adjust before speeding up. “Bet his dick is thicker than mine too. I'd love to watch you take it.”

 

Castiel is meeting his pace, even in this position he does not let Dean do all the work. Castiel huffs out, “Who says I would take it? Maybe I'd ride him and make him hold on for dear life.”

 

Dean lets out a long groan, “Shit. You know I love it when you power bottom.”

 

Dean’s thrusts become erratic. Castiel goes in for the kill. “Yeah? You like it when I pin your arms above your head and ride you like you're just some fuck toy? You think Benny can handle it? Or would I just reduce him to a writhing, needy mess like I do to you?”

 

“Yes!” Dean isn't going to make it. “Fuck, I can't jerk you off without dropping you…”

 

It is Castiel’s turn to smirk, “You'll make it up to me on Friday.” Castiel lets go of Dean's shoulder with one hand and starts to jack himself. He almost falls off the sweat slick counter. He immediately grabs back onto Dean's shoulder.

 

Dean comes with an unintelligible shout. He thrusts up a few more times before using his last reserves of energy to hoist Castiel further onto the counter as he slips out of him and slumps against him, practically in his lap. Castiel runs his fingers through Dean's hair and drags his nails hard enough for Dean to nuzzle into it. Dean's brain returns after a few minutes. He immediately notices Castiel’s unwavering erection. He sighs, "Shit. I'm sorry, Cas. I don't want to leave you hanging. Want me to blow you?”

 

Castiel chuckles darkly and grips himself. He taps the head of his dick against Dean's cheek several times. “I'd rather paint that pretty face of yours and get dinner.”

 

Dean grins and pushes himself up. “You want to do that here?”

 

Castiel lazily strokes himself, “No. I want you on your knees on the floor.”

 

Dean immediately drops. Castiel hops off the counter and stands in front of him. Dean looks up at him with hazy, post-orgasm eyes, “You want me sitting at attention or leaning back?”

 

Castiel thinks it over. Each position has its benefits and drawbacks. “At attention.” The last three times they did this leaning back, someone ended up with a nostril full of semen. That's decidedly not sexy.

 

Dean keep his eyes open and locked on Castiel’s face. He licks the tip of Castiel’s head then tips back. “You look so fucking sexy when you stroke your cock for me.” Dean opens his mouth wide to give Castiel a place to aim.

 

Castiel still has plenty of precome to slick his hand along without issue. He keeps an even pace and looks down at Dean. "Keep talking, Dean. I want to hear what's on your filthy mind.”

 

Dean actually blushes a little. Dean brings his hands up to Castiel’s hips and rubs his thumbs in circles while Castiel continues pumping. Dean clears his throat, "I love it when you make me your little bitch boy. I wanna drink down all your come. I think about it all the time.”

 

Castiel smirks, "Oh, I know you do. Tell me more.” Castiel starts to quicken his pace.

 

Dean moans, “Today I had to jerk off during my lunch break because I thought I wouldn't see you until late at night. I was gonna pick you apart and make you beg for it.”

 

Castiel groans at that, “What changed your plans?”

 

Dean feels his dick valiantly trying to get back in the game but ignores it. He knows he is too sensitive right now even if he can get it up again. “Couldn’t help it. You know what those pants do to me. They stretch just right over your ass. I'm jealous that I can't just go to work with you and grab at your ass all day long.” Castiel falters. He is going quickly now. “You like that? I think about fucking you over your own desk all the time. I'd stuff your tie in your mouth and try to make you scream loud enough that Hannah hears it through those shitty thin walls anyway. Wouldn't even lock the door.” Dean smirks when Castiel groans at that. He knows Castiel likes the _idea_ of being caught, just not actually getting caught. “How long would you last, huh? Would you try to get it done with quickly so no one came in with some god damn paperwork for you to review? Try being a badass boss after one of them walks in on you revealing yourself for the shameless butt slut that you are!”

 

Castiel grabs onto Dean's shoulder. “Oh God, Dean. Don't fucking stop.”

 

Dean can’t stop even if he wants to. “You'd let me do it, right? Shit. Why stop there? We could go into one of the conference rooms with that freaky camera that follows you -”

 

“Video teleconference -”

 

Dean slaps Castiel’s ass, “Like I give a fuck what it's called! All I care about is bending you over and making you watch yourself be railed on the TV screen. Bet you would - oof -” Castiel starts coming and misjudges the power of the first spurt. It lands around Dean's eye instead of near his mouth. Dean doesn't even care. “Yeah, Cas. Give it all to me!” Dean leans back with his mouth open.

 

Castiel is actually pretty courteous this time. He keeps most of his come concentrated on Dean's chin and the lower part of his cheeks and jawbone. He knows it is going to run down Dean's neck eventually. He loves that. He grabs Dean's hand and guides it to his own dick so Dean can take over. Castiel braces his hands on the counter as Dean sucks him hard. Dean always wants to milk Castiel dry. Castiel humors him until the numbness turns toward pain. “That's enough.” Dean pulls off with a pop and leans back for Castiel to get a better view. Dean looks up at him, trying to look innocent for Castiel’s benefit. “I didn't think you could look any prettier but I was wrong.” Castiel reaches a hand down to Dean. “Come here.” Dean takes the hand and gets up from the floor. Once he is on his feet he crowds Castiel’s space, bracketing his body with his own arms. Castiel gives him a quick peck on the mouth. “We should get cleaned up and order takeout.”

 

“I'll take _you_ out,” Dean is proud of himself.

 

“That doesn't even make sense.” Castiel kisses him again. “I love you.”

 

Dean pulls him in for a lazy kiss. He may occasionally enjoy getting messy, but damned if he isn't going to spread the wealth and make Castiel match him. Dean finally pulls away, “So our shower or the one down here?”

 

Castiel scoffs, "How is that even a question? Upstairs.” He playfully shoves past Dean before reaching behind him to grab Dean's hand. They silently make their way to the master bedroom on the third floor. Dean has spent years improving it, and they both reap the full benefits.

 

Castiel grabs towels while Dean walks over to the shower. Dean wags his eyebrows, “You're joining me, right? Conserve water and whatnot.”

 

Castiel doesn't bother arguing that six shower heads do not save water, ever. He could go for some overtime though. Castiel doesn't answer. He gently backs Dean into the spray and chases a stray water drop down Dean's chest. He grabs a washcloth and soaps it up. Dean steps back and watches, allowing it. Castiel returns and begins washing Dean down with a quiet revelry. Castiel leans up to kiss his cheek as he lathers Dean's chest. He whispers, “Thank you for letting me do this.”

 

Dean smiles, “Yeah, yeah. Don't get used to it.” Castiel continues in comfortable silence before he grabs his shoulders and turns him around. Dean's back gets the same treatment. As Castiel reached his mid back, Dean speaks up again, “I was serious about the Benny thing, by the way. The guy is a mess over this and I think he needs his hand to be held to learn the basics of the whole gay sex thing.”

 

Castiel continues working and hums, “It has been a while since we've had company in the bedroom…”

 

Dean turns and pushes Castiel against the wall, “It never gets old with you.” He smiles down at Castiel, “Even after twelve years, it never gets old.”

 

Castiel smiles back, “Even on a Tuesday night?”

 

Dean kisses him, “Especially on a Tuesday night.”

 

Castiel pulls away first, “I am amenable to inviting Benny over - assuming he's into the idea. Just don't schedule it until January. We've got a lot going on this month.”

 

Dean smirks, “So you agree? He can be our-”

 

“Don't say it.”

 

“He can be our sex intern!” Dean bursts out in laughter as Castiel storms out of the shower. Yep, that joke is not going to die anytime soon.


	2. The Lesson

**Summary for the Chapter:**

> Dean and Castiel make good on their promise.

Dean classifies the next conversation with Benny as “Most Awkward Ever” in his mental filing cabinet. It takes some convincing, but Benny finally relents that he would probably be more comfortable watching and maybe, possibly, participating under the right circumstances. The alternative is for Dean to explain everything in excruciating detail.

 

They agree to go with Martin Luther King weekend. The shop is closed, the club is closed, and Castiel is off that Monday. That makes Sunday perfect for education and football. At least, that's how Dean sold it.

* * *

Benny enters the condo through the front door and removes his shoes. He knows the rules from previous visits. When he gets to the second floor he spots Dean on his phone leisurely walking around the kitchen. Dean gestures to the living room when he sees Benny. Benny cuts through the kitchen and past the bar counter to the plush living room. It has a loveseat and a couch with a chaise attached. Castiel is sipping a drink and flipping through the Sunday paper. Castiel spots Benny as he walks into the room. Castiel’s intense concentration gives way to a warm smile. “Hello, Benny.”

 

Benny shuffles from side to side, “Hey, Cas.”

 

Castiel folds the paper and stands, “Can I get you a drink? You look nervous.” When Benny goes to reply, Castiel adds, “It's okay to be nervous.”

 

Benny clears his throat, “Well, whatcha drinkin’? Mimosa?”

 

Castiel laughs, “No. I'm afraid I needed something much stronger to calm my nerves.” Castiel points to the counter littered with food. “Dean and I agreed years ago that we can get daytime drunk on the weekends as long as there's plenty of food to reheat afterwards when we're too drunk and lazy to cook.”

 

Benny burst out laughing. "Man, that sounds like Winchester logic right there.” Castiel smiles to himself for successfully breaking the initial tension. Benny grabs a pastry off one of the plates, “So this is brunch then?”

 

Castiel replies, "I suppose. I'm drinking some concoction Dean made up. It's got scotch, Drambui, orange juice, and grenadine. I'll make you one if it won't knock you on your ass.” Castiel smirks when he gets a glare from Benny. “Dean is on the phone with his father. He might be a while.”

 

As if on cue both men hear Dean raise his voice in the other room. “For Christ's sake, dad! No. I will not talk to Sam about it!”

 

Castiel chuckles, “Awwww, he was doing so well with that New Years resolution…”

 

“Oh?” Benny didn't know Dean did resolutions.

 

Castiel rolls his eyes, “He had a couple: be more responsible with money, lose weight, eat better, be nicer to his family… I was on board with all of them but that last one would never happen. They have a particular talent for pushing his buttons. He bought a new high end surround system on New Years Day so that one failed too.”

 

Dean shouts on the phone in the other room, “Great! Good for them! Adam and that bitch Ruby can rot in Hell for all I care!”

 

Castiel let out a sigh.

 

Benny leans closer to Castiel, "It's cool if you don't want to tell me, but what the hell happened there? That shit was already going down when Dean and I met. I'm always afraid he'll have an aneurysm if I ask him. You know, based on how worked up about it he gets.”

 

Castiel can see Dean angrily pacing back and forth now. Castiel sighs again, “Sam was living with us when you met him, right?” Benny nods. Castiel takes a moment to gather his thoughts. “Sam went to Stanford on a full ride. It's amazing considering that they grew up in a lower middle class family with a single father in the middle of the United States. He got accepted into law school there too.”

 

Benny interjects, “He's a lawyer now, right?”

 

Castiel continues, "Yes. During his first semester we barely heard a peep from him. Second semester and he calls Dean lovesick and head-over-heels for this woman in his one class… I never trusted it! I thought the whole thing reeked of a woman looking for a lawyer husband. Sam gets picked up with a firm he interned with. They move in together and get married two months later. Then Ruby announces that she's pregnant. It was all very rushed. Long story short, she had been screwing their half brother behind Sam's back and the kid wasn't Sam's. He filed for divorce and was a permanent fixture on our couch for months while it dragged out in court.”

 

Benny didn't even try to hide his shock, “Woah. I knew it was cheating that broke up Sam's marriage. I didn't know it was with family. Dean hadn't even mentioned -”

 

Castiel jumps in, "They had different mothers. Adam didn't grow up with them. He was a teenager when he met Sam and Dean for the first time. After Dean found out about what went down Dean disowned him. John will attempt to patch it up, especially around the holidays. You’re right not to ask him. The only time I worry about his blood pressure is when that topic comes up.”

 

Benny let that settle in. “Sam's got a new lady now, right?”

 

Castiel smiles, “Jody. Dean is extremely suspicious of her. Given the circumstances, I would be too.”

 

Benny takes the drink Castiel made for him, “What do you think of her?”

 

Castiel responds, "I like her. I see no problems with her, other than her choice to drink white wine out of a box at room temperature.” He takes a long sip of his own drink, “What about you? I hear that some boy is the reason we’re doing this in the first place…”

 

Benny nearly chokes on his drink, “What? No, not a boy! What did Dean tell you anyway?”

 

Castiel laughs, “Relax. It’s an expression. He said someone hit on you at the club and you decided to go with it.”

 

Benny rolls his eyes, “Oh, so he stopped halfway through the story. Great. I’ll fill in the gaps: got hit on, let him blow me, nothing came of it. Another guy kind of saw some of the kid flirting with me and hit on me the next night. We’re sort of seeing each other, I guess.”

 

Dean storms into the room and shoves the phone in Castiel’s face, “Talk to him! I need a minute.” He pours himself a scotch and slams it back before even seeing if Castiel took the phone. He turns to Benny, “Hey, sorry about that. Family stuff. You know.”

 

Benny raises his glass to Dean, “All too well, brother.”

 

Dean seems to be cooling down, “Once Cas is done smoothing things over we can get down to why you’re really here.” He wags his eyebrows at Benny for emphasis.

* * *

Once John is off the phone the three sit down at the kitchen counter to discuss the ground rules. Benny knew this part was coming. Dean takes a deep breathe and starts, “First off, is there anything that is a show stopper for you?”

 

“I ain’t kissing either of you.” Benny is quick to respond.

 

Castiel replies sarcastically, “That’s a shame.”

 

Dean adds, “Your loss.”

 

Castiel interjects, “No leaving bruises on me. I don’t care, personally, but Dean gets jealous after the fact if he has to look at them. I don’t like it when he is upset.”

 

Dean mumbles, “I do not.”

 

Benny continues, “And I don’t want you touching my dick or my ass, Dean.”

 

Dean mocks offense and Castiel laughs. Dean speaks, “Fine. When we get down to it though, Cas calls the shots. He says a word that even sounds like ‘stop’ and you stop. Got it?”

 

Benny nods. “Fair enough.”

 

Dean continues, “Castiel is used to bottoming, but for educational purposes we’re going to act like he’s not. I know you haven’t banged a dude before, but even you know that sex with a dude is different.”

 

The three sit in silence for a few moments. Dean and Castiel weren’t going to initiate things. They didn’t want to feel as if they pressured him at this moment. Benny finally breaks the silence, “So are we doing this or what?”

 

Dean jumps up from his chair. “Thought you’d never ask!”

 

Castiel stands, “We should make our way to the bedroom.”

 

Dean rolls his eyes, “Yeah, we don’t need the neighbors complaining again.”

 

Benny couldn’t resist the bait, “Again?”

 

Dean barks out a laugh, “Oh yeah, latest was when we had sex on the counter a few weeks ago. Don’t look in our windows if you don’t want a show…”

 

Castiel clears his throat but says nothing. Instead he makes his way to the stairs. Dean and Benny are on his heels. When they get to the bedroom Benny notices that the room was meticulously arranged to be for easy cleanup. The bed was stripped except for a top sheet and a few pillows. There was a chair somewhat near the bed but not directly next to it. Benny also noticed the rather large tube of lubricant and rows of condoms on the nightstand to the left of the bed.

 

Castiel wastes no time once Dean shuts the door. He gives Benny a stone cold look, “Benny, strip.” He looks over at Dean, “Dean, come here. I’m feeling neglected.”

 

Benny hesitates. Dean claps him on the shoulder on his way past, “I’d do what he says. He doesn’t get distracted easily.” Castiel grabs him by the waist and pulls him into a brutal, possessive kiss. Both men work in sync to pull at each others’ clothing and break apart only to cast shirts aside. When they crash back together there appears to be more of a power struggle. They are fighting over who will dominate this one. Benny is still standing stunned watching the entire thing unfold. Castiel shoves Dean’s sweatpants down just past his ass and lets them fall to the floor. Dean, in the interest of saving time, decided to go commando. Castiel growls into the kiss as his hands wander over Dean’s body. Dean pushed a hand into Castiel’s pants and strokes him. It is becoming increasingly obvious that Castiel is winning.

 

Castiel breaks away from the kiss and casts a glance over to Benny, “You’re overdressed.” Dean took it as an opportunity to trail kisses down Castiel’s neck to his collarbone. Castiel pushes Dean away slightly, “Are we overwhelming you?”

 

Benny’s mouth is dry. It takes him a moment to find words, “No. I mean, yes, but in a good way.”

 

Castiel’s stone cold badass face returns, “Good. Frankly, kissing is almost the same whether it’s men or women. Only difference is sometimes there’s facial hair.”

 

Dean wraps his arms around Castiel’s waist from behind and hooks his chin on Castiel’s shoulder. He nuzzles into Castiel’s face. “Okay, so kissing is a no-no in your book. I know you need to know about sex but with two guys there’s a lot more…” Dean had to think of the word, “options.”

 

Benny is still stunned, “I’m not sure I know what you mean…”

 

Dean rubs his hands up and down Castiel’s flanks, occasionally dipping into the waistband of his pants. “Well that part isn’t the same as girls. You can do blow jobs, jerk off, jerk both of you off at the same time, anal… it’s not strictly necessary for, well, you know –“

 

“Penetration. Jeez Dean, just learn to say it.” Castiel huffs.

 

Dean scoffs, “I just don’t like the word, Cas. It sounds too clinical.” Dean looks back at Benny, “So what is it exactly you want to do with whatshisname? You looking to do the whole shebang or something else?”

 

Benny replies nervously, “He’s been pretty patient about this whole thing. I’d like to do everything if I can… from what you were talking about I have an idea of how everything works, either from women or from knowing what I like. It’s the whole anal sex thing that’s got me nervous.”

 

Castiel softens his demeanor, “Do you want us to slow down or jump right into it?”

 

Benny is quick to respond, “Jump in. I’m nervous enough, I don’t need time to over think it.”

 

Dean laughs lightheartedly, “You’re gonna need to ditch some of the clothes, buddy.”

 

Castiel turns to Dean and places a quick kiss on his chin before walking to the nightstand. He grabs a condom and another object that Benny couldn’t quite see. Benny casts his shirt aside, unbuckles his pants and steps out of them. He leaves his boxers for now. Castiel sits on the edge of the bed and takes off his pants as Benny disrobes. Castiel gives himself several sure strokes then rolls on the condom. He is fiddling with the other item he picked up earlier. Dean catches Benny eying it with confusion. Dean clarifies, “It’s a cock ring. We’ve done this whole educational thing before. The last student got a little overzealous with some of Cas’ sweet spots and got him to blow his load early. We’re not risking a repeat… not that making him come is a bad thing but that’s not why we’re here.”

 

Benny is still looking at the cock ring as Castiel fastens it. “You guys use those things often?”

 

Dean shrugs, “Not really. We’ll use it with each other if we’re doing something slightly kinkier. Again, not like a girl, we are lucky is we can go three times in a day. Those things just drag it out. It makes coming a lot more intense once it finally does happen.”

 

“Huh.” Benny makes a mental note to research the pros and cons of cock rings. No way in hell is he trusting Dean ‘Oh come on it’s not that spicy’ Winchester on whether or not they’re good just on his word alone.

 

Dean walks over to the nightstand, takes a condom, and rolls it on. Once he is done he grabs another one and flicks it onto the bed in Benny’s direction, “If you leave your boxers on you don’t have to use it, but the second they come off that goes on. Not negotiable.” Dean cups Castiel’s face and kisses him again quickly; he can’t stop himself. He looks back to Benny, “So there’s really two beginner positions where you’d start prepping from: with him on his back or on his stomach or hands and knees. On his back you’d usually be making out or blowing him at the same time. On his stomach you can still do a reach around as long as he’s not being lazy on you.”

 

Benny looks perplexed again, “Which is, uhhhh, easier?”

 

“Easier how?” Dean absently picks up the lubricant as he asks.

 

Benny thinks it over, “Easier for him. Like the most comfortable.”

 

Castiel laughs, “Lesson One: it always feels a little uncomfortable. It’s something going into your body that you don’t have control over. That doesn’t mean it hurts but it always feels a little uncomfortable to start with.” He looks at Dean, “I think hands and knees is probably easier for demonstration purposes.” He looks back at Benny, “Gauge what he wants though. Sometimes I just want Dean to get it done quickly, other times I want him to distract me. Kissing is a really, really good distraction.” Dean takes the hint and kisses him one more time before Castiel gets on his hands and knees.

 

Dean lets out a low whistle, “I never get tired of that view, angel.” Benny snickers at the pet name. Dean shoots him a glare but climbs on the bed. “You can watch from back there but you’d probably be better off saddling up here.”

 

Benny tries not to check Castiel out too much while he shuffles next to Dean. Sure, both men were attractive but he really is here to learn. Benny points to the tube in Dean’s hand, “I assume that’s got a lot to do with what comes next.”

 

Dean beams, “Man, this is your new best friend! No offense, Cas.”

 

Cas laughs, “None taken.”

 

Dean pops the cap on the tube. He spares a glance at Benny, “Breathe buddy. It’s sex, not brain surgery.” Dean spreads a generous amount of lube on his fingers and rubs his fingers together. “You want to warm this stuff up. It’ll ice cold otherwise.” Dean swipes some over Castiel’s hole. Castiel tenses beneath him; Dean puts down the tube and places a hand on the small of Castiel’s back. “You want to start with one finger and work up from there. Cas is usually good with two or three. Others might need more stretching.” Dean slides a finger in with little effort. He pumps it a few times before intentionally crooking it. The action rips a keen from Castiel. “Prostate is another great distraction but proceed with caution. Some guys beg for it when you stimulate it while others beg you to stop because it’s overwhelming.” Dean adds a second finger and pumps them in and out a few times. He separates his fingers a few times, watching Castiel become more open for him. “You want to scissor your fingers to make more room. That way you can add another. Don’t be afraid to add more lube.” Benny had a studious look about him, like he was trying to take notes but was overwhelmed by the facts. Dean has a wicked thought out loud, “You wanna give it a try?”

 

Benny sputters, “What? No, I mean, Castiel is your husband…”

 

Dean reminds himself to be patient, “My husband and I invited you over for an educational threesome. You can watch but you’re more than welcome to touch. We’ve done this before.” Benny tentatively reaches for the lube. He puts some on his fingers and mimics Dean’s previous actions. Dean removes his fingers from Castiel and lets Benny press one finger in tentatively. Dean lets him slowly slide it in and out a few times. “Do you know how to find the prostate? Like have you tried it on yourself?”

 

Benny looked at him oddly, “On myself? No.”

 

Dean continues, “It’s sort of similar to the G-spot. Just crook your finger and you’ll just kind of know when you found it. Usually the reaction will tell you what –“

 

Castiel keens again, “Shit, Dean!”

 

Dean smirks, “See? You’re already a pro! And don’t be offended. He usually only says my name.”

 

Benny repeats the action a few more times. “Is he good for another?”

 

Castiel pipes up, “Yes.”

 

Benny blushes, “Sorry Cas.” Benny makes up for it when he pushes another finger in. Dean groans loudly, and god damn if he wasn’t right! Castiel felt like he had three of Dean’s fingers with only two of Benny’s fingers.

 

Dean leans over to rub Castiel’s shoulders. Dean turns back to Benny, “So are you planning on fucking him or are you gonna leave me hanging?”

 

Castiel adds, “He really likes the idea of you taking me while he watches.”

 

Dean quickly jumps in, “But not until you’ve got at least three fingers in him!”

 

Benny pushes a third finger in as if Dean’s statement is a challenge. Castiel lets loose a low, guttural moan. Benny gasps, “Shit,” almost to himself.

 

Dean stares with fascination as Benny continues to finger Castiel. Castiel is pushing back into it. He looks ready to Dean. He certainly sounds ready. Dean leans over to Benny, “Now or never. I can’t let you tease him forever.”

 

Benny gets off the bed and kicks his boxers off. Dean gives Castiel a triumphant smile. Benny rolls on the condom left on the bed and kneels on the bed. “Is what we did enough or…”

 

Dean knows where he is going with that. “I always use more lube on my dick before going in. And just because he’s stretched doesn’t mean he’s ready. He will need some time to adjust. When in doubt, just ask him.”

 

Benny nods and slicks himself up. Dean unconsciously holds Castiel’s hand as Benny presses against his entrance. Dean and Benny both groan at the sight of Benny’s cock disappearing into Castiel. Castiel squeezes Dean’s hand; Dean is unsure if it’s out of discomfort or to reassure him. Benny gets about halfway when he asks, “You good Cas?”

 

Castiel croaks, “Don’t stop until you’re all the way in.”

 

Dean groans loudly at that and Benny complies. Benny braces over him panting, “God, you’re tight.”

 

“You can move.” Castiel squeezes Dean’s hand again. Benny pulls out most of the way and slams back in. It punches the air out of Castiel. Despite his earlier reservations, Benny starts a rough, hard pace. Castiel pants Dean’s name over and over as he meets Benny’s pace. Dean begins to jerk himself as he watches. Both men are surprised when Castiel sits up, pushes an arm against Benny’s chest, and says, “Stop.”

 

“What’s wrong?” Dean immediately inquires.

 

Castiel scoots forward and Benny slips out of him. “We need to do a different position. This one isn’t doing it for me.”

 

 _Oh no, he’s actually going to do it_ , Dean thought.

 

Benny is concerned, “Where do you want me?”

 

Castiel casts a dark look at him, “On your back in the middle of the bed.” Benny scrambles to comply. Castiel gives him a critical, assessing look when Benny waits. “Your penis is curved in a way that makes doggy style less than ideal. You’ll want to do this or missionary with your mystery man if you want to get him off.”

 

Dean rolls his eyes, “Way to be blunt about it.”

 

Castiel grips Benny and sinks down onto him. His eyes roll back until he is fully seated. Benny rests his hands on Castiel’s hips as Castiel begins to move in a circular motion. He is having sex with Benny but his eyes are glued on Dean. The only warning Benny gets is a slight glint in Castiel’s eye. Castiel grabs both of Benny’s hands and slams his hands to the mattress above his head. He pulls them together and holds them down as he starts bouncing up and down. Dean starts jerking himself off in earnest. Castiel builds up to a fast pace and Benny breaks his hands free. Castiel slams them back down. Castiel growls, “Dean, hold his arms down!”

 

Benny keens. He is completely at Castiel’s mercy, and apparently the man has none. Dean, of course, is quick to comply. Dean finally begs, “Benny, please tell me it’s ok to straddle you! I gotta get closer to him.” Benny has no words left. He nods in an exaggerated up and down motion. Dean temporarily lets go of Benny’s wrists to straddle his chest.

 

Castiel immediately pulls Dean flush against him and sucks hard on Dean’s neck. He wants to mark the man. Dean hunches forward to hold Benny’s wrists down. Castiel starts bouncing again. He lets his hands roam all over Dean’s body. Dean moans every time Castiel’s dick rubs between his butt cheeks. No one is surprised when Benny comes first. Dean lets go of him and reaches behind himself to pop the cock ring off Castiel. It only takes a few strokes to push Castiel over the edge. Dean wants to make sure Benny knows what it is like to have a guy orgasm while a dick is still in him. Dean quickly gets off of Benny so Castiel can readjust himself. He slides off Benny and slumps forward on the edge of the bed panting.

 

When Benny catches his breath he notices that Dean is still hard, “Shit, sorry you didn’t get off.”

 

Dean chuckles, “I’m sure you’ll come up with a way to make it up to me.” Dean thwacks the head of his dick against the side of Benny’s face. Benny groans and grimaces in response.

 

“Dean!” Castiel hates it when Dean does that, even when he’s not on the receiving end.

 

Dean points to the bathroom, “Whenever you’re ready, there’s a fantastic – one time only – offer to clean up in our shower. Cas left clean towels out for you.”

 

Castiel inquires, “By the way, what is whatshisname’s name anyway?”

 

Benny hazily replies, “Cole.”

* * *

After the best shower of his life, Benny finds his clothes already gathered and folded on the bed for him. When he makes his way downstairs he sees Castiel and Dean cuddling together on the couch. Dean lounges on the chaise while Castiel presses as close as possible to his side, possibly dozing. Dean is in sweatpants and a tee shirt; Castiel is in the same with a bathrobe over it. Dean spots Benny and waves him over, “Hey grab a drink! Kickoff is in six minutes.”

 

Benny is confused, “So you want me to stay?”

 

Dean scoffs, “Only if you want to, man. I know you’ve got money on this game too! You might as well stay.”

 

Benny sits and finally breaks the silence after a few minutes on a commercial break. “Is this a thing you guys do? It doesn’t change anything else about your friendships?”

 

Castiel sleepily replies, “Not really. We’ll do it once in a while, but only with people we trust.”

 

Dean smiles, “What he said.” He takes a sip from his drink. “We usually don’t play with the same people twice, but we might make an exception for you and Cole…” He looks down at Castiel, “This one is always taking applications for sex interns.”

 

Castiel groans, “I really wish you would let that go.”

 

Dean gloats, “Can’t. Giving you hell is one of my resolutions this year.”

 

… It’s gonna be a long year.

**Notes for the Chapter:**

> If the drink Castiel was sipping on in Chapter 2 sounded familiar you have probably seen the [Avengers themed drinks](http://www.tipsybartender.com/blog/the-avengers-cocktails).

**Author's Note:**

> Comments, constructive feedback, and kudos are appreciated. They make me smile down in my dark, depraved soul.


End file.
